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Deuteration of verapamil by acid catalyzed exchange
Author(s) -
Nelson Wendel L.,
Bartels Michael J.
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210211
Subject(s) - chemistry , verapamil , moiety , ring (chemistry) , hydrogen–deuterium exchange , catalysis , antagonist , deuterium , stereochemistry , calcium channel , medicinal chemistry , calcium , organic chemistry , hydrogen , receptor , biochemistry , physics , quantum mechanics
Deuteration of verapamil, 5‐[(3,4‐dimethoxyphenylethyl)methyl‐amino]‐2‐(3,4‐dimethoxyphenyl)‐2‐isopropyvaleronitrile, an important calcium channel antagonist was accomplished by direct exchange in 25% 2 H 2 SO 4 in 2 H 2 O. Refluxing for 140 hr incorporated 4–6 atoms of deuterium, which were distributed into both aromatic rings, but primarily in the ring attached through position 5 of the valeronitrile moiety.